Multi-step reaction with 13 steps
1.1: NaH / tetrahydrofuran / 0.25 h / 0 °C
1.2: 70 percent / tetrahydrofuran / 1.5 h
2.1: NaBH4 / methanol; 2-methoxy-ethanol / 0.33 h
2.2: 51 percent / DMAP / CH2Cl2 / 24 h
3.1: 89 percent / Sn(OAc)2; (i-Pr)2NEt / dimethylformamide / 17 h / 80 °C
4.1: H2; AcOH / PtO2 / 5 h / 20 °C
5.1: 59 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 3 h
6.1: 96 percent / sulfur trioxide pyridine complex; triethylamine / dimethylsulfoxide / 48 h
7.1: 82 percent / AcOH / H2O / 96 h / 25 °C
8.1: 79 percent / 4-dimethylaminopyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH2Cl2; dimethylformamide / 3 h
9.1: HCl / dioxane; H2O / 2 h
10.1: HATU; (i-Pr)2NEt / dimethylformamide / 20 h
11.1: Et2NH / Pd(PPh3)4 / tetrahydrofuran / 0.25 h
12.1: 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 4 h
13.1: CF3CO2H / CH2Cl2 / 2 h
With
hydrogenchloride; dmap; sodium tetrahydroborate; hydrogen; tin(II) acetate; sulfur trioxide pyridine complex; sodium hydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
platinum(IV) oxide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2-methoxy-ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo034837z